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Hydrocortison
CORTISOL · HYDROCORTISONE BASE · HC · HYDROCORTISONEACETATE · Hydrocortisone - CAS 50-23-7 - Calbiochem · Hytone · H-Cort · Cortril
Identifikatoren & physikalische Daten
| CAS No. | 50-23-7 |
|---|---|
| Summenformel | C21H30O5 |
| Durchschnittliche Molmasse | 362,5 g/mol |
| Monoisotopische Masse | 362,20932406 g/mol |
| SMILES | C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO |
| InChIKey | JYGXADMDTFJGBT-VWUMJDOOSA-N |
| PubChem CID | 5754 |
| ChEMBL | CHEMBL389621 |
| ChEBI | CHEBI:17650 |
| EC No. | 200-020-1 |
| DTXSID | DTXSID7020714 |
| Lokaler Name | Hydrocortison |
Chemische & physikalische Eigenschaften
| XLogP | 1,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 94,8 |
| H-Brücken-Donoren | 3 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 26 |
| Formalladung | 0 |
| Komplexität | 684 |
| Stoffklassen | Pharmaceutical |
| Arzneimittel | Pharmaceuticals -> SteroidsPharmaceuticals -> Listed in ZINC15 |
| Lipide | Lipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203] |
| SpringerMaterials Properties | Crystal structure |
| LogP (Verteilungskoeffizient) | log Kow = 1.61 |
| Geruch | Odorless |
| Geschmack | Bitter taste |
| Color/Form | Plates from alc or iso-propyl alcCrystalline, striated blocks from absolute ethanol or isopropanolWhite, crystalline powder |
| Löslichkeit | Amorphous, hygroscopic, white powder. Mp 169.0-171.2 °C. Solubility in water: approx 500 mg/mL. Similarly soluble in methanol, ethanol,sparingly soluble in chloroform. /21-Sodium succinate/Solubilities in various solvents [Table#4538]Soluble in concentrated sulfuric acid with intense green flourescenceSoluble in dioxaneIn water, 320 mg/L at 25 °CH2O: 100 mg/mL319.7mg/L(25 ºC) |
| Human Drugs | Breast FeedingLactationMilk, HumanCorticosteroids, SystemicGlucocorticoidsAnti-Inflammatory AgentsCorticosteroids, TopicalFDA approved drugs -> Active ingredientEMA approved medicines: Human medicine |
| Animal Drugs | Active Ingredients (Hydrocortisone) -> FDA GreenbookPharmaceuticals -> Animal Drugs -> Approved in Taiwan |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Schmelzpunkt | 211-214 °C(lit.) |
| Siedepunkt | 414.06°C (rough estimate) |
| Dichte | 1.0812 (rough estimate) |
| Brechungsindex | 1.6120 (estimate) |
| Flammpunkt | 220°C |
| Lagerbedingungen | -20°C |
| Aggregatzustand | powder |
| Farbe | White |
| pH | 5.0- 7.0 |
| Biologische Quelle | non-animal source |
| Decomposition | 220 ºC |
| Merck | 14,4787 |
| BRN | 1354819 |
| Henry-Konstante | 1.7×102 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Stable, but may be light sensitive. Incompatible with strong oxidizing agents. |
| Hauptanwendungen | clinical testingclinical testing |
| InChIKey | JYGXADMDTFJGBT-VWUMJDOOSA-N |
| SMILES | C[C@]12CCC(=O)C=C1CC[C@H]3[C@@H]4CC[C@](O)(C(=O)CO)[C@@]4(C)C[C@H](O)[C@H]23 |
| LogP (Verteilungskoeffizient) | 1.610 |
| CAS Datenbank | 50-23-7(CAS DataBase Reference) |
| NIST chemische Informationen | Hydrocortisone(50-23-7) |
| EPA chemische Informationen | Hydrocortisone (50-23-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 1.1% (3 of 274) of reports.WarningH361 (86.5%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]P203, P260, P280, P318, P319, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 274 reports by companies from 34 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Pregn-4-ene-3,20-dione, 11,17,21-trihydroxy-, (11.beta.)-Status: Active Update: 06-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14486Hydrocortisone: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Pregn-4-ene-3,20-dione, 11,17,21-trihydroxy-, (11.beta.)-: Human health tier I assessment |
| FDA-Anforderungen | The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl hydrocortisone valerate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Hydrocortisone Valerate/The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl hydrocortisone butyrate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Hydrocortisone Butyrate/The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl hydrocortisone acetate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Hydrocortisone Acetate/The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl hydrocortisone, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.For more FDA Requirements (Complete) data for HYDROCORTISONE (9 total), please visit the HSDB record page. |
| Hazard Classes and Categories | Repr. 2 (86.5%) |
| Lagerbedingungen | Commercially available preparations of hydrocortisone should be stored at a temperature less than 40 °C, preferably between 15-30 °Cfreezing of the oral suspension and sterile suspensions should be avoided. Hydrocortisone tablets should be stored in well-closed containers. Reconstituted solutions of hydrocortisone sodium succinate should be stored at 25 °C or below. |
| Allowable Tolerances | A tolerance is established for negligible residues of hydrocortisone (as hydrocortisone sodium succinate or hydrocortisone acetate) in milk at 10 parts per billion. |
| Wechselwirkungen | Hydrocortisone (80 mg/kg body weight, intraperitoneally for 4 days), both alone and in combination with acetylsalicylic acid (160 mg/kg body weight, orally, for 4 days), decreased acetylsalicylic acid general and specific toxicity via metabolic modulation of drug-metabolizing enzyme systems (intestinal acetylsalicylic acid-esterase and hepatic UDP-glucuronyltransferase) and did not change the acetylsalicylic acid analgesic effect.The effect of glucocorticoids on oral anticoagulant therapy is variable, and the efficacy of oral anticoagulants has been reported to be enhanced or diminished with concomitant glucocorticoid administration. Patients receiving glucocorticoids and oral anticoagulants concomitantly should be monitored (e.g., using coagulation indices) in order to maintain desired anticoagulant effect. /Corticosteroids/Estrogens may potentiate effects of hydrocortisone, possibly by increasing the concentration of transcortin and thus decreasing the amount of hydrocortisone available to be metabolized.Potassium-depleting diuretics (e.g., thiazides, furosemide, ethacrynic acid) and other drugs that deplete potassium, such as amphotericin B, may enhance the potassium-wasting effect of glucocorticoids. Serum potassium should be closely monitored in patients receiving glucocorticoids and potassium-depleting drugs. /Corticosteroids/For more Interactions (Complete) data for HYDROCORTISONE (7 total), please visit the HSDB record page. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 180(SRC), determined from a log Kow of 1.61(2) and a regression-derived equation(3), indicates that hydrocortisone is expected to have moderate mobility in soil(SRC). Volatilization of hydrocortisone from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.8X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Hydrocortisone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.3X10-13 mm Hg(SRC), determined from a fragment constant method(5). Biodegradation data were not available(SRC, 2007).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 180(SRC), determined from a log Kow of 1.61(2) and a regression-derived equation(3), indicates that hydrocortisone is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 5.8X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2007).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), hydrocortisone, which has an estimated vapor pressure of 1.3X10-13 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase hydrocortisone may be removed from the air by wet or dry deposition(SRC). Hydrocortisone does not absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(5). |
| Soil Adsorption/Mobility | The Koc of hydrocortisone is estimated as 180(SRC), using a log Kow of 1.61(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that hydrocortisone is expected to have moderate mobility in soil. |
| Human Toxicity Excerpts | /SIGNS AND SYMPTOMS/ Glucocorticoids should be used with caution in patients with seizure disorders, renal insufficiency, osteoporosis, or herpes simplex infections of the eyesome manufacturers state that glucocorticoids should not be used in patients with active ocular herpes simplex infections /SRP: due to the risk of corneal ulceration/. /Corticosteroids//CASE REPORTS/ A 66-year-old man who complained of generalized muscle weakness, shallow respiration, and palpitations after receiving high-dose intravenous hydrocortisone (total dose, 2400 mg over 4 days) to treat a severe asthma attack /is described/. During this therapy, there was a weight gain of 1.0 kg. An electrocardiogram revealed ventricular arrhythmia with frequent premature ventricular contractions. Hypokalemia was profound, with plasma potassium (K+) concentration of 1.7 mEq/L, and associated with renal potassium wasting, as evidenced by a transtubular potassium concentration gradient of 12metabolic alkalosis (plasma hydrocortisone O3-, 37 mEq/L) was also present. When treated with spironolactone, KCl supplementation, and substitution of hydrocortisone with prednisolone, his plasma K+ concentration rapidly normalized, metabolic alkalosis was corrected, and arrhythmia disappeared within 3 days. Because of unwanted mineralocorticoid side-effects, high-dose hydrocortisone may cause life-threatening hypokalemia in asthmatic patients. Because of these potential risks, plasma acid-base and electrolyte concentrations should be monitored frequently in any patient treated with high-dose hydrocortisone./CASE REPORTS/ A 62-year-old asthmatic patient with evidence of aspirin sensitivity ... /was/ administered 100 mg of hydrocortisone-21-hemisuccinate dissolved in 100 mL 0.9% sodium chloride solution for perioperative corticoid substitution. The patient immediately developed severe bronchospasm and anaphylactic shock requiring intubation and mechanical ventilation. He received adrenaline, isoflurane, ketamine and inhalational fenoterol. He then developed atrioventricular block type III for which he was transcutaneously paced. Subsequently he was tested via skin prick tests, intracutaneous tests and IV-challenges resulting in the patient having positive reactions to hydrocortisone-21-hemisuccinate. /Hydrocortisone-21-hemisuccinate//CASE REPORTS/ Glucocorticoids may indirectly cause convulsions by the induction of electrolytes abnormalities, severe hypertension, or severe hyperglycemia. These agents may rarely cause convulsions by a direct toxicity to the central nervous system (CNS). We describe a 23-yr-old patient with Crohn's disease in whom generalized convulsions developed on two occasions while receiving intravenous hydrocortisone.For more Human Toxicity Excerpts (Complete) data for HYDROCORTISONE (8 total), please visit the HSDB record page. |
| Artificial Pollution Sources | Hydrocortisone's production and use as an antiinflamatory(1) may result in its release to the environment through various waste streams(SRC). |
| Drug Induced Liver Injury | Drug-Induced Liver Injury Severity and Toxicity (DILIst)hydrocortisoneDILI NegativeOralDOI:10.1016/j.drudis.2019.09.022 |
| Environmental Bioconcentration | An estimated BCF of 3 was calculated in fish for hydrocortisone(SRC), using a log Kow of 1.61(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for hydrocortisone is estimated as 5.8X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that hydrocortisone is expected to be essentially nonvolatile from water surfaces(2). Hydrocortisone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.3X10-13 mm Hg(SRC), determined from a fragment constant method(3). |
| Non-Human Toxicity Excerpts | /LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ The effects of hydrocortisone during the prenatal period and its later repercussion on reproductive aspects of female rats /were investigated/. Pregnant rats were treated (s.c.) with hydrocortisone acetate, at 1.5 mg/day on the 17th, 18th, and 19th days of pregnancy. Although the present study was not intended to identify mechanisms of toxicity, the treatment with hydrocortisone in the last period of pregnancy presented no signs of toxicity. The efficacy of the hydrocortisone in reducing the adrenal wet mass and plasma corticosterone levels immediately after delivery in both the treated mothers and in respective pups at birth may indicate impairment of the hypothalamus-pituitary-adrenal axis. In addition, the treatment with hydrocortisone did not interfere in the development of the female descendants until puberty. However, it affected the estrous cycle and fertility. Probably, the prenatal exposure to corticosteroids had altered at least partially the hypothalamus-pituitary-gonadal axis, resulting in the damages observed in adult life. These results indicate that the use of the hydrocortisone at a dose that apparently does not endanger the neonate led to undesirable effects in the adult reproductive phase, resulting in later deleterious alteration of the reproductive physiology in female rats. /Hydrocortisone acetate//LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ The aim of the present study was to investigate the effects of hydrocortisone during the prenatal period and its later repercussions on the fertility and sexual behavior of male rats. Pregnant rats were treated (sc) with hydrocortisone acetate, at 1.5 mg/day on the 17th, 18th, and 19th days of gestation. Decreased body weight and no alteration in anogenital distance were observed in male offspring. Adulthood, presented reductions of body weight, plasma testosterone levels, and seminal-vesicle wet weight without secretion as well as no alteration in the wet weights of the testes, epididymis, and seminal vesicle with secretion in the treated group. Males exposed to hydrocortisone during the prenatal period were able to mate with normal females, which became pregnant but exhibited an increased number of post-implantation losses. In spite of this, these treated males exhibited decreased male sexual behavior and the appearance of female sexual behavior after these male rats were castrated and pretreated with exogenous estrogen. These results indicate that exposure to hydrocortisone in the later stages of pregnancy may have a long-term effect on the fertility and sexual behavior of male rats, suggesting an incomplete masculinization and defeminization of the central nervous system. |
| Populations at Special Risk | Because cortisone has been reported rarely to increase blood coagulability and to precipitate intravascular thrombosis, thromboembolism, and thrombophlebitis, corticosteroids should be used with caution in patients with thromboembolic disorders. Glucocorticoids should be used with caution in patients with seizure disorders, renal insufficiency, osteoporosis, or herpes simplex infections of the eyesome manufacturers state that glucocorticoids should not be used in patients with active ocular herpes simplex infections. /Corticosteroids/Because an apparent association has been suggested between use of corticosteroids and left ventricular free-wall rupture after a recent myocardial infarction, corticosteroids should be used with extreme caution in these patients. /Corticosteroids/This study examined the hypothesis/ that subjects with posttraumatic stress disorder, as compared to nonpsychiatric controls, would show greater impairments in verbal declarative memory and working memory, but not attention, following exogenous glucocorticoid administration. ... The hydrocortisone administration led to impairment in working memory in the group of subjects with posttraumatic stress disorder, but not in the control subject group. |
| Environmental Abiotic Degradation | Hydrocortisone is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze readily under environmental conditions(1). Hydrocortisone does not absorb at wavelengths >290 nm(2) and therefore is not expected to be susceptible to direct photolysis by sunlight(1). |
| Probable Routes of Human Exposure | NIOSH (NOES Survey 1981-1983) has statistically estimated that 36,900 workers (21,576 of these are female) are potentially exposed to hydrocortisone in the US(1). Occupational exposure to hydrocortisone may occur through inhalation and dermal contact with this compound at workplaces where hydrocortisone is produced or used(SRC). Use data indicate that the general population may be exposed to hydrocortisone via dermal contact with this compound and other consumer products containing hydrocortisone(SRC). |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29372100 |
| RTECS-Nr. | GM8925000 |
| R-Sätze (R) | 62-63 |
| Toxizität | LD50 subcutaneous in mouse: > 500mg/kg |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 36/37 |
| Lagerklasse | 3 - Flammable liquids |
| Gefahrstoffdaten | 50-23-7(Hazardous Substances Data) |
| Gefahrenklasse | Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1 |
Anwendungen & Verwendung
Verwenden
Cortisol, or Hydrocortisone, is a steroid hormone, more specifically a glucocorticoid, produced by the zona fasciculata of the adrenal gland. Cortisol is released in response to stress and a low level of blood glucocorticoids. Its primary functions are to increase blood sugar through gluconeogenesis; suppress the immune system; and aid in fat, protein and carbohydrate metabolism.